Redirect boss’s interest into social connection, activities

Advertisement

Advertise with us

DEAR MISS LONELYHEARTS: My boss is a lovable nerd — not socially connected at all. He absolutely adores me, and trots around behind me at work, like a puppy. He’s in his 40s and still a bachelor. He’s very well-to-do, and would love to be married and have a family.

Read this article for free:


or

Already have an account? Log in here »

To continue reading, please subscribe:

Subscribe and receive a limited-edition Free Press branded hat or tote.

Digital Subscription

One year of digital access for only $205*

  • Enjoy unlimited reading on winnipegfreepress.com
  • Read the E-Edition, our digital replica newspaper
  • Access News Break, our award-winning app
  • Play interactive puzzles

*First annual payment billed as $205.00 + GST for one year. This annual subscription will automatically renew at $233.00 + GST every 52 weeks (10% off the regular annual price of $259.35). Offer available to new and qualified returning subscribers only. Cancel any time.

To continue reading, please subscribe:

Add Free Press access to your Brandon Sun subscription for only an additional

$1 for the first 4 weeks*

  • Enjoy unlimited reading on winnipegfreepress.com
  • Read the E-Edition, our digital replica newspaper
  • Access News Break, our award-winning app
  • Play interactive puzzles
Start now

*Your next Brandon Sun subscription payment will increase by $1.00 and you will be charged $17.95 plus GST for four weeks. After four weeks, your payment will increase to $24.95 plus GST every four weeks.

Opinion

Hey there, time traveller!
This article was published 06/03/2023 (1256 days ago), so information in it may no longer be current.

DEAR MISS LONELYHEARTS: My boss is a lovable nerd — not socially connected at all. He absolutely adores me, and trots around behind me at work, like a puppy. He’s in his 40s and still a bachelor. He’s very well-to-do, and would love to be married and have a family.

I’m in my 30s, divorced and have three kids at home. But I’m not interested in him at all.

On Valentine’s Day, my boss gave me a joke card, but I could see through the joke to the man who’s dying for a wife and family. I started to feel badly, although I certainly don’t flirt with him. I could never be that cruel.

My work skills are in high demand, and my best friend thinks I should consider getting another job and get the heck out of there. She thinks his crush on me is not healthy for either of us. What do you think?

— Getting Pressured, North Kildonan

Dear Pressured: You don’t need to give up your job, but you do need to tell your boss gently: “It’s not going to happen for us as a couple.” But then, you could also tell him you’d be willing to help him meet a bunch of fun, new people.

If he agrees, however reluctantly, tell him you’re going to help him do some research online into local activities-based singles groups. He could also look into joining groups for social, recreational or creative pursuits that interest him, or even explore opportunities to volunteer that can facilitate healthy connections.

There’s also a national group online called Meetup, found at meetup.com. They offer many more activities that are showcased online. Many people who join different activities are single, but not necessarily. They’re just people with common interests, getting together to try different activities, and it’s mainly a place to meet new people and make buddies with similar tastes.

If you volunteer to act as your boss’s activities coach, and get him out living a fun lifestyle, you might also discover different activities from his that call to you — and you’ll meet some new friends yourself. You know you probably need to!

Dear Miss Lonelyhearts: I like your advice to the jealous husband in Tuxedo.

That’s the man whose wife is getting big raises and is now making more money than he does. (I told him that when his wife becomes pregnant, he’ll have a heavy financial burden to carry for a time, so he should be glad his wife is earning good money and investing it now to help support the family. —Miss L.) I want to add to that advice.

This man should know it’s a statistical truth that divorce rates spike when wives begin to earn more than their husbands. My advice to him — as someone who has been through it — is to start looking for ways to either supplement his income or pick up a respectable side-project/hobby which his wife can feel pride in, and respect him for it.

Maybe he can start thinking of ways to provide her gifts she likes, or show in other ways that he’s still a man who can take care of her, or their community/family members, as a provider. I wish him good luck.

— Experienced in this Situation, Winnipeg

Dear Experienced: Thanks for writing. Happily, you’ve managed to cope with this jealousy problem yourself and work through it. Hopefully, the man who wrote in will be able to use some of your suggestions.

It must be said that not every man feels the need to be the major provider, and not every woman wants her mate to be that. In fact, some men are great at running a home and relieved not to have to be “out there.”

Still, it can be difficult for any family in this expensive world if one of the parents is totally out of paying work or still studying full-time and not bringing in any money. It’s hard to make ends meet for many people these days.

Please send your questions and comments to lovecoach@hotmail.com or Miss Lonelyhearts c/o the Winnipeg Free Press, 1355 Mountain Ave., Winnipeg, MB, R2X 3B6.

Maureen Scurfield

Maureen Scurfield
Advice columnist

Maureen Scurfield writes the Miss Lonelyhearts advice column.

Our newsroom depends on a growing audience of readers to power our journalism. If you are not a paid reader, please consider becoming a subscriber.

Our newsroom depends on its audience of readers to power our journalism. Thank you for your support.

History

Updated on Monday, March 6, 2023 8:48 AM CST: Fixes byline

Report Error Submit a Tip

More Stories

Mom grieves loss of daughter, 4, on Long Plain First Nation

Morgan Modjeski 3 minute read Preview

Mom grieves loss of daughter, 4, on Long Plain First Nation

Morgan Modjeski 3 minute read Tuesday, Aug. 11, 2026

The mother of a four-year-old girl killed and two other children injured on Long Plain First Nation said she raised concerns about their care months before her daughter’s death.

Read
Tuesday, Aug. 11, 2026

City charter ties council’s hands in wake of criminal allegations against Transcona councillor

Joyanne Pursaga 5 minute read Preview

City charter ties council’s hands in wake of criminal allegations against Transcona councillor

Joyanne Pursaga 5 minute read Yesterday at 6:12 PM CDT

In the wake of additional criminal charges laid against Transcona Coun. Russ Wyatt, several council members say the city should explore options to impose leaves of absence on elected officials who face serious allegations in the future.

Wyatt, 56, was charged Monday with sexual assault and administering a noxious thing with intent to aggrieve or annoy in relation to an October 2023 incident. The councillor was previously charged with sexual assault and administering a noxious substance in March, based on allegations tied to a 2025 gathering.

Under the City of Winnipeg charter, a provincial law, a member of city council automatically forfeits their seat if they are convicted of certain serious criminal offences. It does not apply if they are simply charged.

Mayor Scott Gillingham and others have urged Wyatt to step away from his city hall duties voluntarily, while Gillingham has also suggested the province review the legislation.

Read
Yesterday at 6:12 PM CDT

A Winnipeg home with a mountain view? You won’t find a real one, but AI-generated visual suggests otherwise

Gabrielle Piché 6 minute read Preview

A Winnipeg home with a mountain view? You won’t find a real one, but AI-generated visual suggests otherwise

Gabrielle Piché 6 minute read Tuesday, Aug. 11, 2026

Manitoba’s mountain range peeked out behind a Scotia Street home.

At least, it did in a photo attached to a real estate listing for 232 Scotia St. in Winnipeg’s (flat) Seven Oaks neighbourhood.

Another picture — now removed — showed a cartoon cityscape viewable from the bungalow’s front porch.

Both photos had tags in their bottom left corners: “AI-generated content.”

Read
Tuesday, Aug. 11, 2026

Talent of Blue Bombers’ Ceresna shines through all the way from Div. 3

Taylor Allen 5 minute read Preview

Talent of Blue Bombers’ Ceresna shines through all the way from Div. 3

Taylor Allen 5 minute read Yesterday at 7:45 PM CDT

Jake Ceresna looks exactly how you’d imagine a professional football player would.

The 6-5, 290-pound defensive end for the Winnipeg Blue Bombers has a hulking, broad-shouldered frame built on a pair of tree-trunk legs.

But considering where he came from, it’s rather remarkable that he’s been giving opposing quarterbacks nightmares in the pros for a decade.

For starters, he hails from New Fairfield, Conn. The list of pro football players from the town of approximately 14,000 people starts and ends with Ceresna.

Read
Yesterday at 7:45 PM CDT

Manitoba to pitch Churchill at investment summit

Free Press staff 1 minute read Preview

Manitoba to pitch Churchill at investment summit

Free Press staff 1 minute read Yesterday at 6:49 PM CDT

Manitoba will pitch its Port of Churchill Plus project to global banks and sovereign wealth funds next month.

Premier Wab Kinew said the project — which includes upgrades to the deepwater Churchill port — will be “in the deal book” being presented at the Canada Investment Summit.

The inaugural summit in Toronto, slated for Sept. 14 and 15, is set to draw investors such as Berkshire Hathaway and JPMorgan Chase & Co., the world’s largest bank, The Globe and Mail reported.

Prime Minister Mark Carney is hosting the summit in partnership with the Canada Pension Plan Investment Board and the Public Sector Pension Investment Board.

Read
Yesterday at 6:49 PM CDT

Boyd Group hits US$1 billion sales in a quarter

2 minute read Preview

Boyd Group hits US$1 billion sales in a quarter

2 minute read Yesterday at 6:52 PM CDT

The company behind Boyd Autobody & Glass cracked $1 billion in sales within a quarter — the first time it’s done so in its 36-year history.

On Wednesday, Boyd Group Services announced sales of US$1.013 billion for its second quarter. It’s a 29.9 per cent increase from the year prior.

Over that year, Boyd Group Services added 340 new locations. Those sites added $211.3 million to its overall sales and accounted for most of the growth.

Same store sales grew 2.9 per cent.

Read
Yesterday at 6:52 PM CDT